Coming Up With Good Story Ideas Is Hard: Here Are Some Brainstorming Tips

From a post on by Matt Crossman headlined “Brainstoming tips for Freelancers”

I am often asked where my ideas come from. I joke that coming up with ideas is easy. Coming up with good ideas is hard. Coming up with ideas good enough to sell? That’s extremely difficult….

Sometimes ideas pop into my head unprompted and I’m at a loss to explain where they came from. More often, my ideas come because I intentionally seek them out. Brainstorming is essential to that. Here’s how I do it.

Set aside time for it

I don’t follow a strict schedule of, say, brainstorming every Tuesday at 1 p.m. or anything like that. I block off a few hours on my calendar a day or two in advance, use that time to come up with a whole slew of ideas at once, sell as many of them as I can, work on them for a while and then start over. Some days, for reasons I can’t explain, I feel drawn to brainstorming. I indulge that feeling when it hits me….

Clear your mind, put your phone on airplane mode, move your body

I do my best brainstorming when I’m either hiking or riding my bike. I go to familiar trails/routes because when I hike or ride on an unfamiliar route, I use up valuable brain power in following the trail and absorbing my surroundings.

Before the hike or ride starts, I decide which client I will brainstorm for. I think about recent stories I have written for them, conversations I’ve had with the editors, and any other foundational issues (lead time, style of writing, how they use art, etc.) to get me thinking about the target publication. Once I start moving, I focus on ideas. My brain flits around, of course, but I try to catch an idea and examine it as closely as possible.

Use prompts

To kickstart my brainstorming, I often ask my editors questions. What kind of story haven’t you had that you want? Or what theme issues do you have coming up that I can think of ideas for?

For my sports clients, anniversary research is an endless source of ideas.

What do I want to learn about

I am a Theodore Roosevelt fanboy, so I sold two stories about visiting the area of North Dakota where he once lived. I’m fascinated by organ transplant, so I have written several in-depth stories about it….

What’s on my bucket list

I learned by selling a story about trying to get my first hole-in-one that a successful bucket list idea requires brainstorming two things at once. There’s what the story is about, lowercase, which was trying to get a hole in one. And there’s what the story is ABOUT, uppercase, which was persevering toward a hard goal. (Full credit, I first heard the two explanations from Tommy Tomlinson, a friend who is an extraordinary writer.)

Those ideas aren’t going to remember themselves

I used to carry a notebook with me everywhere I went so I could jot down ideas when they occurred to me. I’ve stopped doing that only because I use my phone instead and send myself emails. I leave them unopened so they stay at the top of my queue until I do something with them—either pitch them or ditch them. I’ve heard of writers who keep notebooks next to the shower because they get so many ideas in there. You can also try Indy’s tasks tool to keep track of all your ideas. Write each idea down as a task and leave it until you do something with it.

Review your previous work

Think of past ideas like stepping stones. By standing on one, you can plot what your next step will be. Ask yourself two questions: How can I make another rock similar to this one? And where can I go from this rock? If you’re a clothing designer, maybe that means fashioning pants to go with your most recent shirt. If you’re a novelist, maybe it’s a sequel or a spinoff.

The best example I have of this is the brainstorming I did after I wrote about the crazy things NHL dentists see. After that was published, I pursued two separate tracks, each of which answered one of the above questions.

After I asked myself, where can I go from this rock? I sold a profile of one of the NHL dentists to his alumni magazine.

After I asked myself, how can I make another rock similar to this one? I profiled the doctor who travels with the Professional Bull Riders and the physician’s assistant who takes care of NASCAR drivers and pit road crew members. Next up, I hope: The people who work in the medical tent at Tough Mudder, Spartan races, and other obstacle course events.

Imitation is flattery … and a productive way to brainstorm

I got an email newsletter from a financial planner about a month ago. The subject line was something like, “The To-Don’t List for Investors.” My first thought was, that’s a clever subject line. My second thought was, how can I borrow it? I quickly brainstormed ideas. I settled on a story that would fall under the headline, “The To-Don’t List for Freelancers,” which I turned into an assignment for this publication. There’s a line between borrowing and stealing. Don’t cross it.

Reward yourself

This is difficult but crucial work. The rewards — the solid story, the paycheck, the acknowledgement of a job well done — don’t come until much later. I “pay” myself for good ideas. If I come up with something I’m fairly certain will sell, I’ll extend my hike or bike ride so I can keep enjoying the outdoors, or treat myself to a mocha on the way home, or knock off work early and take my kids to the park.

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